Winerid hentrich and max hardtmann



Patented Nov. 4, 1930 wmrrunnnn'rarcrr VAND MAX HARDTMANN, or wrnsnonr-onrrrn-nnmn; nn

RUDOLF. KNOCI-IE,: on LEvnRKUsEn-on-rnE-anmn GERMANY," 'Ass rGNoRsflTo GENERAL ANILINE worms, mo, or NEW YORK, n. Y., A CORPORATION or DELA- WARE CONDENSATION raonucr on THE zennz onrnz mn snares No Drawing. Application filed March 8, 1928, Serial No. 260,239, and in- Germany March 18, l927.: 1

The present invention concerns new condensatlon products of the benzodlazlne ser1es and the process of producing the same.

They most probably have the general for 5 mula:

I' & i-0R2): l. V v

wherein R stands for an aromatic residue, which is attached to the diazine nucleus through a carbon atom, R stands for hydrogen which may be replaced. by alkyl and a: stands for one of the numbers one and two.

Our new compounds can be prepared by any of the customary processes for producing a carbon-carbon-linkage, e. g. by heating together benzodiazine which is substituted in the diazine nucleus by halogen with a substituted or not substituted phenolic body in the presence of aluminium chloride, or by heating together a benzodiazine which is substituted in the diazine nucleus by halogen with a halogenated phenolic body in the presence of an alkali metal. Otherwise our new compounds may be prepared by causing suitable aromatic magnesium halogenide compounds, e. g. alkoxy phenyl magnesium bromide in ethereal solution to react upon halogenated benzodiazine containing the halogen in the diazine nucleus.

Our new products are generally high melting or not melting yellowish powders which are insoluble in water, soluble in organic solvents with a yellowish coloration. The

products, either as such or after further treatment, are intended to be used for the most varied purposes, for example, as intermedfiate products in the manufacture of dyestu s.

The following examples will illustrate our invention, which, of course, is not in any Way restricted thereby:

Example 1=-145 parts by weight of l-hydroxynaphthalene are dissolved in 1000 parts of tetrachlorethane, 100 parts by weight of QA-dichloroquinazoline are added and gradually 160 parts by weight of powdered anhydrous aluminium chloride. The mixture is heated for an hour to90-100 C; and worked 0 up as customary. The resulting yellowish" powder is the 2.4-di( lf-hydroxynaphthyl) quinazoline chars at 240-250" C. withoutmelting. It dis-' solves'in concentrated sulfuric acid with an V 5 It can be recrystallized from alcohol. It

intense violet coloration, from thissolution 7 N% possessing the melting point 280-23? C. is obtained. It dissolves in concentrated sulfuric acid with a violet blue coloration. I

Example 3.To 211.5 parts by weight of mulat y prepared in the customary manner dissolved of 4-chloroquinazoline and the whole is stirred for two hours at a temperature of 30-40 C. Them the magnesium-chloridebromide is filtered Ofi'. From the concentrat- .para-anisol-magnesium-bromide'of the for-1 p in benzene are added 1 64.5 parts by weight sfe antes I line of the pr'obableformula u 1 I Process for producing new "*condnsation products ofithe benzodiazine series,

which process comprises causinga' halogen 7 an intense violetcoloration 1 v 1111;test mony whereof we have;

beinga yellowish powder, insolulole' wa ter', solub1e in alcohol with a yellowish coloration andinconcentrated sulfuricsacid with ated benzodiazine containingsatz-least one:

uponan g aro natic phenolic. compound in'vthe' pre'sence ofaalifminiuin chloride. V 2:;Proee'ssg'forrproduomgi new condensa- 4 .1 1-, r 5

I halogen atom in the diazinenucleus to freact '15 tion products of the fbenzodiazinepseries;

" which process comprises; causing 2.4-di

chloro-benzodiazine to reactupon l-hydroxynaphthalene in the presenceof aluminium chloride.

I v yellowi'sli color'ation;

3. As new products' conipounds of the probable general foi 'nnulalzx:

amok I V wherein 3 R5 stands "for an aromatic residue,

which is; attached I to} the diazine' nucleus through a; carbon atom R stands for hydrogen whicli may beiiepIaced' by'aIkyI and'w stands for one of theynumbersone and two, being generally high melting or'notmelting i'eunto yellowish powders, which are unsoluble-in r water; soluble inorgan c 'solventswithfa, i

" 4.'As1.new "productscompounds of the rpbable-formula s "wherein R stands for anaphthalene residue, I "whlch is attached to the diazine nucleus as through a carbonat0m,R stands foi' hydr0-' l g gen which may be replaced by alkyl and a; x

stands fon one of f the numbers one andtwo,

7 being; gener-allyhigh melting or" not melting Y yellowish powders,- whioh are insoluble in watersoluhle zin norganic solvents with a yel w zcb w t o -i.

V "5. 'Asa new product 2.4;di- (4 -hydi'oxynaphthyl)-qui nazoli'ne' "li ise 

